Efficient synthesis of enynes by tetraphosphine-palladium-catalysed reaction of vinyl bromides with terminal alkynes

Tetrahedron

Volumn 62, Issue 1, 2006, Pages 112-120

  Feuerstein, Marie ^a   Chahen, Ludovic ^a   Doucet, Henri ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Alkynes; Catalysis; Palladium; Sonogashira; Vinyl bromides

Indexed keywords

ALKYNE DERIVATIVE; BROMIDE; PALLADIUM; PHENYLACETYLENE; PHOSPHINE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SONOGASHIRA REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 28444445923     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.124     Document Type: Article

References (44)

1. M. Bujard, F. Ferri, and M. Alami Tetrahedron Lett. 39 1998 4243
2. E. Negishi, and L. Anastasia Chem. Rev. 103 2003 1979
3. A.M. Gomez, A. Pedregosa, A. Barrio, S. Valverde, and C. Lopez Tetrahedron Lett. 45 2004 6307
4. K. Sonogashira Metal-Catalyzed Cross-Coupling Reactions F. Diederich P.J. Stang 1998 Wiley New York
5. K. Sonogashira J. Organomet. Chem. 653 2002 46
6. L. Brandsma, S.F. Vasilevsky, and H.D. Verkruijsse Application of Transition Metal Catalysts in Organic Synthesis 1998 Springer Berlin
7. W.A. Herrmann, C.-P. Reisinger, and M. Spiegler J. Organomet. Chem. 557 1998 93
8. D. McGuinness, and K. Cavell Organometallics 19 2000 741
9. V.P.W. Böhm, and W.A. Herrmann Eur. J. Org. Chem. 2000 3679
10. T. Hundertmark, A. Littke, S. Buchwald, and G. Fu Org. Lett. 2 2000 1729
11. M. Buchmeiser, T. Schareina, R. Kempe, and K. Wurst J. Organomet. Chem. 634 2001 39
12. D. Alonso, C. Najera, and C. Pacheco Tetrahedron Lett. 43 2002 9365
13. A. Köllhofer, and H. Plenio Chem. Eur. J. 9 2003 1416
14. K. Heuzé, D. Méry, D. Gauss, J.-C. Blais, and D. Astruc Chem. Eur. J. 10 2004 3936
15. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467
16. V. Ratovelomanana, and G. Linstrumelle Tetrahedron Lett. 22 1981 315
17. M. Alami, F. Ferri, and G. Linstrumelle Tetrahedron Lett. 34 1993 6403
18. G. McGaffin, and A. Meijer Synthesis 1994 583
19. J. Kabbara, C. Hoffmann, and D. Schinzer Synthesis 1995 299
20. G.T. Crisp, Y.-L. Jiang, P.J. Pullman, and C. Savi Tetrahedron 53 1997 17489
21. W.-W. Dai, and A. Wu Tetrahedron Lett. 42 2001 81
22. X. Fu, S. Zhang, J. Yin, and D.P. Schumacher Tetrahedron Lett. 43 2002 6673
23. T. Lomberget, D. Bouyssi, and G. Balme Synlett 2002 1439
24. M.G. Organ, H. Ghasemi, and C. Valente Tetrahedron 60 2004 17489
25. U. Halbes, P. Bertus, and P. Pale Tetrahedron Lett. 42 2001 8641
26. A. Mori, T. Shimada, T. Kondo, and A. Sekiguchi Synlett 2001 649
27. W.P. Gallagher, and R.E. Maleczka Jr. J. Org. Chem. 68 2003 6775
28. T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, and I. Ryu Org. Lett. 4 2002 1691
29. J.P. Genet, and M. Savignac J. Organomet. Chem. 576 1999 305
30. S. Caddick, F.G.N. Cloke, G.K.B. Clentsmith, P.B. Hitchcock, D. McKerrecher, L.R. Titcomb, and M.R.V. Williams J. Organomet. Chem. 617-618 2001 635
31. Y. Ma, C. Song, W. Jiang, Q. Wu, Y. Wang, X. Liu, and M.B. Andrus Org. Lett. 5 2003 3317
32. M. Alami, B. Crousse, and F. Ferri J. Organomet. Chem. 624 2001 114
33. L. Wang, and P. Li Synth. Commun. 33 2003 3679
34. D. Laurenti, M. Feuerstein, G. Pèpe, H. Doucet, and M. Santelli J. Org. Chem. 66 2001 1633
35. M. Feuerstein, H. Doucet, and M. Santelli J. Org. Chem. 66 2001 5923
36. M. Feuerstein, D. Laurenti, C. Bougeant, H. Doucet, and M. Santelli Chem. Commun. 2001 325
37. M. Feuerstein, F. Berthiol, H. Doucet, and M. Santelli Org. Biomol. Chem. 2003 2235
38. M. Feuerstein, F. Berthiol, H. Doucet, and M. Santelli Synthesis 2004 1281
39. M. Feuerstein, H. Doucet, and M. Santelli Tetrahedron Lett. 46 2005 1717
40. M. Feuerstein, H. Doucet, and M. Santelli Tetrahedron Lett. 45 2004 8443
41. M. Feuerstein, H. Doucet, and M. Santelli Tetrahedron Lett. 45 2004 1603
42. M. Lemhadri, H. Doucet, and M. Santelli Synthesis 2005 1359
43. K. Okuro, M. Furuune, M. Enna, M. Miura, and M. Nomura J. Org. Chem. 58 1993 4716
44. See Ref. 7 in: T. Hayashi, K. Kabeta, I. Hamachi, and M. Kumada Tetrahedron Lett. 24 1983 2865